17 Iconic Celebrity Outfits That Everyone Has Been Talking About

Jimmy Henton

An outfit might be just an outfit, but it can also be more. It can spread tales about a relationship or reveal a person's political opinions to the world. And it can be a manifestation of one's individuality or simply a gossip to get people talking. However, these expressions of fashion really shine when a famous star does it.
Celebrities hold tremendous influence over American fashion on the red carpet, in the cinema, and on the stage. Garments like Marilyn Monroe's classic white dress in "The Seven Year Itch" have become cultural touchstones that embody the art of the era throughout Entertainment history. What’s more, when you look at images of singers and movie stars, you quickly realize that fashion is a baffling thing: what looked amazing ten years ago may now be hilarious. Regardless of how fashion changes, the celebrities who wore those items remain fashionable.
From Old Hollywood to the present, here are 17 celebrity fashion moments that have sparked debate over the years.

#1 Halle Berry and her swoon-worthy James Bond outfit

Source: © Die Another Day / 20th Century Studios


#2 Lizzy Gardiner wore a credit card dress in 1995

Source: © Ron Galella / Ron Galella Collection / Getty Images


#3 Priyanka Chopra and her epic Met Gala gown, which required two attendants and one bus

Source: Charles Sykes / Invision / AP / East News, Charles Sykes / Invision / AP / East News


#4 Cardi B and her Aphrodite-stepping-out-of-a-shell Grammys gown

Source: Gilbert Flores / Broadimage / Broad Image / East News


#5 Madonna in her boy-toy attire at the 1984 MTV Video Music Awards

Source: ASSOCIATED PRESS / East News


#6 Angelina Jolie and her revealing black vinyl dress

Source: © Mr. & Mrs. Smith / 20th Century Studios


#7 Cher in her transparent black Oscar gown in 1988

Source: AP / East News


#8 Gwyneth Paltrow and her controversial 2002 Vanity Fair Oscar gown

Source: Mary Evans / Allstar / Graham Whitby Boot / East News


#9 Lara Flynn Boyle and her ballerina outfit in 2003

Source: Courtesy Everett Collection / East News


#10 Princess Diana with her stunning silk slip floor-length gown at the 1996 Met Gala

Source: © Steve Eichner / WireImage / Getty Images


#11 Barbra Streisand with her see-through gown at the 1969 Academy Awards

Source: ASSOCIATED PRESS / East News


#12 Anne Hathaway and a contentious Oscar gown from 2013.

Source: John Shearer / Invision / AP / East News


#13 Kim Basinger and her Frankenstein-like Oscars gown with Cyrillic characters on her sleeve in 1990

Source: © Alan Light / Wikimedia Commons© CC BY 2.0


#14 Rihanna with her provocative gown in 2011.

Source: KENNELL KRISTA / SIPA / East News


#15 Zendaya with her silver breastplate dress from 2020

Source: Hahn Lionel / ABACA / Abaca / East News


#16 Brad Pitt in a skirt during a film premiere

Source: babiradpicture / RalfMuelle / SIPA / SIPA / East News


#17 Jordan Roth and his gleaming appearance in 2022

Source: Invision / Invision / East News